


One Night, On Valentine's Day

by amazingAisha16387



Category: The Vampire Diaries (TV)
Genre: Two shots Valentine's Day special.
Language: English
Status: Completed
Published: 2020-02-14
Updated: 2020-02-15
Packaged: 2021-02-27 23:35:05
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,999
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22724026
Author URL: https://archiveofourown.org/users/amazingAisha16387/pseuds/amazingAisha16387
Summary: Elena friend Rebekah arranged a male escort for her on Valentine's Day. There, she was approached by handsome guy who stole her breath away and maybe her heart.
Relationships: Elena Gilbert/Damon Salvatore
Comments: 4
Kudos: 12





	1. Man With Red Rose.

**Author's Note:**

> Special Notes.
> 
> Happy Valentine's Day to all you lovely readers out there. Since I am eternally single for me my readers are my valentine and just for you special people I present you my first ever two shot story. I really hope you enjoy it.

"This is a bad idea." She told herself as she walked towards the hotel bar that was decorated with same heart shape balloons like the rest of the hotel.

Elena Gilbert is not your average single girl who is searching for love especially on Valentine 's Day. In fact, she is one of those girls that lost faith in love and everything related to it a decade ago when she got divorced only after six months of her marriage.

Her sudden divorce shattered her self esteem and for a while, she was just existing aimlessly. She isolated herself completely from everyone, even her family and close friends were unable to bring back that fun, loving, beautiful and smart girl she once was.

It was only four years ago her life gets a little bit better when she befriended her new boss Rebekah Mikaelson.

Elena still couldn't understand why they are friends? Because her personality is totally opposite from her friend who has the power to make people gravitate around her, but then again not only she looked like a runway model but also has a most charming personality that makes everyone fawn over her.

"You can do a lot better than being friends with dull boring Elena." She told her one evening when Rebekah dragged her to the party.

"You don't give yourself much credit Gilbert. Maybe you need to get laid to change your dour personality."

Hence began Rebekah nonstop attempts to hook her up with one guy or another but Elena turned everyone down because after Liam, her Ex-husband who breaks her heart for another woman, she starts distrusting man species.

She was so bitter that even thought of being with man creeps her out.

She found the alternative solution of her loneliness in fictional men who are brave and kind, loyal romantic and passionate. She knew it was insane but in her mind, she can fantasies them as much she wants and since they are not real they won't break her heart.

Rebekah thought she was crazy to refuse a real experience over her imaginary world but this was something Elena wouldn't budge on.

"At least do something productive with this imaginary shit! Your fantasy men are so hot and passionate so why don't you write about them?"

Elena has to admit that this idea changes her life because now she is a successful author of four bestseller novels.

She was surprised how many girls like her were out there and for once she was glad to bring happiness in their lives through her books.

Still, there was a low moment of her life when fantasy was not enough. There were times when she craves a romantic relationship.

Someone kind and gentle who can make her feel special. Who can hold her in his arms and make her feel wanted in those lonely hours?

But whenever she found the courage to date again her old doubt's return with full force and once again she stepped away from her desires and went back to the same pattern of her life.

This year she was extra depressed because it marks not only one decade of her failed marriage but also a dry spell she has been in for the last ten years.

"That's it! No friend of mine can live without sex for a decade! I wish I could find your Ex and castrated him to destroy such a beautiful young girl like you."

"Its Thirty-three years old woman you are feeling sorry for." Elena slurred as she finished another bottle of red wine.

"I just wish I haven't gotten married at such a young age! I thought Liam was my perfect life partner but he perfectly destroyed my heart that now I doubt anyone can ever repair it."

Elena then burst into tears while Rebekah did her best to comfort her depressed friend.

"You know what? If you can't do relationship then at least find someone to hook up with you?"

But this brings more tears into her eyes as she finally confesses something that she would never admit to herself in her sober mind. "I don't know the first thing to seduce a guy! Even thought of conversing with any guy makes me self conscious."

Rebekah was ready to pull her hair in frustration and once again curse her friend's Ex who is the reason she would never find the courage to approach another man.

If only there is a way for Elena to interact with a man both physically and emotionally without having any expectations to bring back her old doubts.

For weeks she rattles her brain and even though Elena assure her she was fine, Rebekah won't give up.

She thought hard until finally one day just a few days before Valentine's Day she came up with a brilliant solution to help her out.

"Male Escort Services?! Are you insane!" Elena screams in disgust as Rebekah's hand her a card. "Yes and before you get all angry bird on me, just hear me out."

Elena almost told her no but she gave her a pleading look which makes her gave in. "Okay fine! But my answer is no."

Rebekah rolled her eyes before gently placing her hand on Elena's shoulder.

"You said yourself that it's difficult for you to approach a guy?" She waited for her to acknowledge this problem and when she sadly nods her head she continues. "That's why if you spend one night with male escort then you won't expect anything from that encounter which in return not only gave you chance to get physical pleasure out of it but emotionally unwind you, so next time when you see a guy you really like you will be able to approach him confidently, without any doubts getting in your way."

Elena couldn't help but ponder on her suggestion and the more she thought about it, the more she felt that this can be a solution to solve her problems.

"Okay fine but you will arrange everything. The less I know the better. Just tell me time and place."

Which brings her to this very day that also happens to be Valentine's Day.

She was nervous but hopeful that this One Night, on Valentine's Day will break her inner barrier and maybe she can find her lost confidence again.

With that resolution, she confidently waited for that man.

According to Rebekah he will be dressed in black and approach her with a single red rose.

Looking around she can see many girls in traditional red attire and that's why she specifically chose to wear a short black dress that not only makes her stood out from rest of the crowd but also make it easy for that guy to recognize her.

It was her second cocktail as her eyes search for this guy but so far no one approach her yet. She was itching to call this thing off but since Rebekah knew her so well, she knew that her call will go straight to her voicemail.

Looking around once last time she finished her glass as she starting to feel pathetic. 'This really shows how desperate loser you truly are.' Her inner voice taunts her.

Giving up she was about to leave when a red rose appears in front of her. "Sorry to keep you waiting."

She twirls around on her stool and comes face to face with the most handsome guy who has smouldering blue eyes that were staring deeply at her. "Happy Valentine 's Day. I hope you gave me pleasure to spend this time with you?"

Elena, who was still staring at this guy with wonder could barely manage to nod her head.

Grabbing her wrists he asks her. "Can I ask pretty lady name?"

'Is he real? Or the product of my active imagination?' Elena thought to herself but since she can feel his warm hands she felt sane enough to answer.

"Elena, my name is Elena."

"Its pleasure to meet you, Elena." He then kissed her palm but somehow that kiss went straight to her core. He then lifts his face and gave her a flirty smile as he said. "My name is Damon, Damon Salvatore."

And for the first time Elena was sure about something that no matter what transpired between them today, but from now on this name and guy will be the star of her new fantasies.


	2. Girl In Black.

**Summary for the Chapter:**

> What comes out of their encounter? A total Mess up situation or a great outcome?

Damon Salvatore is not your average guy, who was sitting alone at the bar drinking while searching for some desperate conquest on Valentine's Day. In fact, he knows the power his looks and personality held over the female population and he even used it to his advantage ever since he hit puberty.

Yet as years go by he starts appreciating the female species and in his experience, the more delicate they look, the more strong they are from inside.

That appreciation didn't come to him overnight. It was after he met his wife Rose that he starts to respect and change his opinion about them.

Rose in every sense was the perfect girl for him. He even proposed her within eight months of their dating but she smiled and told him that she will accept his proposal in a few years once they both graduate from their university and were mature enough for marriage.

At first, he was a disappointment but Rose always look ahead of time and she was right to wait because by the time they graduated their relationship was stronger than ever and not only they love each other but now they develop beautiful companionship between them.

After that, they were happily married for five years and when they thought they were ready they decide to have a baby. But not all dreams come true and sadly for Damon the day that was supposed to be the happiest moment of their lives turn the saddest day of his.

Ironically it was the week before Valentine 's Day almost four years ago when his wife went into early labour.

He still remembers how his world shattered when the doctor informs him of his stillborn son and how his wife lives were on the thread because of massive internal bleeding.

His wife was pale yet beautiful as she smiles at the sight of him and her parting words showed him how strong, kind, generous and loving women truly are.

( Flashback)

"Damon, I'm so sorry." He was about to stop her but she continues anyway. "I'm sorry for leaving your life but promise me that you won't let this tragedy destroy your life."

He was in tears unable to make this promise but his wife sees right through him and gave him a sad smile. "You have so much love to give, this heart is big enough to let someone inside and it's my wish that you find love and happiness in your life again."

"I don't know if this heart can love anyone else." He cried out as he can see life slipping away from her eyes but still it gave him a hopeful look. "One day, when you finally found her this heart will automatically guide you to her. Just promise me that when that moment comes you won't shy away from it but instead embrace it with an open heart."

(End of Flashback)

Even in death, she was sure that his heart will find someone else to love and yet four years later he found himself and his heart lonely on the day that supposed to celebrate love.

He was not supposed to be here at first place if it wasn't for a meeting he came to attend on his brother's behalf. Usually, he spends this day with his dog Rex after visiting his wife grave but then he got a call from Stefan who begged him to take his place so he can celebrate Valentine 's Day with his girlfriend Caroline.

He laughed while remembering how his brother begged him and being romantic at heart he was unable to refuse his request.

His eyes fell on Rose and he picked it up while smiling at it. "Happy Valentine's Day Rose."

Kissing its petals he was about to place it back on the vase when his eyes fell on a girl.

He looked around and wonder 'why amongst all these Valentine's crowd a beautiful girl in black is sitting all alone by herself?'

Even her eyes were anxious as they stared around this romantic atmosphere. He was sure that she didn't come here with the same motive as these couples and the way she is fidgeting its seems to him that she wishes to be anywhere instead of this place.

For a second Damon thought that maybe he was wrong in his assessment because this girl is extremely gorgeous and maybe her boyfriend is late but after some time the way her face fell in disappointment, tells him that some idiot stood her up and now like him she is here all alone.

He felt sorry for this girl and a little bit angry that a girl like her is being let down by some prick on a day when every girl dream to be cherished.

Suddenly the rose that he was twirling around his fingers slipped on the table and the way it fell it was pointing straight to that girl.

"Rose." He breathed his wife name as his gaze filter from the flower to the girl its pointing and at the same time something shift inside his heart.

"This is a strange way to guide someone." He told the Rose as he picked it up but in his mind, he can see his wife winking at him from great beyond.

Bracing himself he walked towards that girl and hoped that he won't make fool out of himself.

############

After introducing each other Elena wonder what she supposed to do with this gorgeous specimen?

She can see he was about to suggest to begin their night but she quickly asks. "Can I offer you a drink?

Damon who was about to do the same shut his mouth in surprise. 'Don't be a surprised idiot! Women have equal rights to offer a drink.' He scolds himself and the more he thought he thinks its kind of flattering.

"Sure. Bourbon is my poison." He then settles down on the seat beside her and Elena felt glad to buy some time to compose herself.

Damon watched as she orders their drinks with little shaky voice. 'Maybe she is getting nervous to be with a stranger.' He thought and decides it better assure her. "Don't be nervous because I'm too." He whispered in her ear.

Ignoring the shiver his voice cause, Elena blinked her eyes in confusion. 'Why would he be nervous?' She wondered.

"I understand my nerves but I don't see any reason for you to be nervous about this thing."

"This thing." Damon chuckled as he raises his drink. "It's been four years since I did this thing, that's why I am nervous because I am scared to mess up with your expectations."

While he sipped his drink Elena wonders if Rebekah selected him for this very reason. Because if she considers his four years lack of prostitution absence is nothing compared to her ten years of abstinence from sex.

Damon watched her sighing in relief as she drinks her cocktail with relax smile. "I'm glad you told me that. You have no idea how happy this makes me."

She clicked their glass and downed hers in one gulp. "Ah! I'm so ready now. Come let's take this party to my room."

"What!?" Damon didn't understand how his lack of dating experience led him straight to this girls room. 'Rules of the first date, sure enough, change over the years.' He thought while figuring out a way to stall her. "What about dinner because I'm sure." He was suggesting to take her out for dinner but apparently, he said the wrong thing because she scowls at him.

"Are you hungry? I thought the only drink was enough but if you want…" She is not miser, if this guy wants food before giving her sex then she can at least buy him dinner.

Damon felt embarrassed by her question and quickly backtrack. "No, no! I am not hungry, I mean we can go for dinner later, there is no rule that says…" He trails of feeling more embarrassment.

Elena, on the other hand, though he was cute and she gently grabbed his hand to assure him. "Of course we can get dinner later. You can even pick your favourite cuisine."

She was glad when he smiled and nodded his head. She then stood up and tugged his hand. "Come, I'm staying at this hotel."

He wants to tell her that his apartment is also a few blocks from here but then stopped himself as he thought. 'Maybe she will be more comfortable in her own room?'

So he let her lead the way. Both quite nervous as they tried to see anything instead of each other. He almost jolts with the ding of the elevator but then she stepped out and he followed her leaving his nerves behind.

Elena gasp when she felt a warm hand on the back of her dress. It was a miracle she didn't trip but somehow managed to open her room door.

It was a nice room, she left side lamp on to give this room a dim glow. He watched as she dropped her clutch and rose on the side table before turning around to face him.

Once again he was taken by her beauty but he noticed her shy eyes and nervousness make her extremely adorable in his eyes.

Elena clearly didn't know what to expect but what she didn't expect was him to cup her face and kiss on her forehead. "Breath."

He felt air escape from her mouth as her doe-like eyes watched him with fascination. He then kisses her eyelid, her cheeks even tip of her nose that brings a smile on her face but then he was about to kiss on her lips when she stops him.

"Not on lips."

He felt it strange but he would never push her to do something she is not comfortable with. He was about to put stop on this whole thing when she turned around and pulled her hair on one side to reveal her zip. "Can you unzip me."

Elena saw his disappointment when she stopped him to kiss her, he even backs away from her and for a second she thought to call this thing off but then an angry voice scream in her head. 'Don't be a cowered Gilbert!' So she quickly turned and ask him to unzip her.

She waited for what felt like an eternity but could be a minute when finally he slowly starts unzipping her dress and to Elena, that act felt more erotic than she ever thought.

She moaned when soft hands caress her back.

Damon was surprised and turned on when he saw no bra underneath her dress. He watched as she slipped off her dress and reveal black thong gracing her tanned legs.

Without turning around she walked shakily towards the bed and then laid down on her back.

Elena took a deep breath with closed eyes before opening them. She saw how mesmerized he was as he watched her almost naked, spread out on the bed. Its seems he was waiting for instructions to do his job, so she musters a strong voice as she commands him. "Strip for me."

Damon has to blink a few times to clear his head because he was uncertain about how this nervous beauty suddenly transform into a seductive dominatrix.

To his surprise, she leaned over her elbow and stared at him from top to bottom with a heated look. "Strip now Mr Salvatore, or I will call this thing off."

She starts laughing how quickly he starts obeying her because in less than a minute he was standing naked in front of him. She had to bit her lip when her eyes roam over his hot, sexy body. Especially his hardened members that is quite impressive in her opinion.

She watched as he slowly approaches her, he then kissed her foot and she mewls like a kitten as his lips trail upward her body.

He was beyond turned on by her soft noises, his member was achingly hard and leaking by the time he kissed her inner thigh before stopping right there as he asks. "Can I kiss these lips?"

For a moment she was confused but then she felt her thong being removed and then his finger trailing over her women hood. "Here. Can I kiss you here?"

"Yess!" She hiss when he pumps that finger inside her and soon his lips join to make her scream in pleasure.

"Oh! Uhhh!" She moaned as her hips thrust upwards while her hands reached out to hold his hair.

She didn't know what soft thing she was yanking for support because her eyes are gone cross-eye when his tongue start thrusting inside her. With a jolt, she realizes that he was eating her out like one of her fantasy and damn! the real thing ruined that fantasy for her.

"I, I!" She gasps and he smiles against her skin as he lifts his face to order her. "Let go." He then resumes licking her again and a few seconds later her sweet nectar filled his mouth while she screamed in pleasure.

Elena was sure she has gone blind but then slowly her senses begin to appear as she came down from her pleasurable high. She couldn't help but smile with Damon who was watching her with a smug look on his face. "Not bad for a guy who lacks four years of experience."

He watched as she kissed back of his palm, her eyes held something like gratitude as she says. "You are great, no for me, you are simply best because you just rock this girl life who is experiencing her first real sexual encounter in ten years."

The moment these words were out they both gasp in shock. Elena felt extremely embarrassed to confessing this humiliating secret.

Meanwhile, Damon still finding it hard to wrap his head around this truth. "You mean? No one? How?" He felt like an idiot but he really wanted to understand.

Apparently, Elena was not in the mood to discuss this anymore because she suddenly covered herself with sheets and moved to sit. "I'm sorry to say that stuff, I know it's not supposed to be part of the deal."

"Fuck the deal! You didn't have sex in ten years!" He shouts out with wide eyes.

"Were you living in blind colony for a decade or something? because a gorgeous girl like you can bring any man down on his knees with just one look."

He was extremely serious but she starts laughing. "You are just saying that because."

"Because of its fucking truth!" He exclaimed and she believes that he is not humouring her because of his job.

"You are really sweet and nice." Too sweet for an escort. " I am glad of being here with you tonight."

To his surprise, she let go of her sheets and lean in to kiss him.

She felt him groan against her mouth and she deepened their kiss while pushing him down so she can straddle him.

He watched with glazed eyes as she grabs his member giving it a few pumps. "Hand me condom from the drawer." She told him while pointing at the side table.

He quickly grabbed one and hand her. He watched her open it with shaking hands, so he grabbed it and put it himself.

"Thanks, she breathed and in next second they both moaned when he slipped inside her wet heat.

"Oh!" Elena felt like her body was an instrument and he was an artist playing her because right now a wonderful melody can be heard in her head.

Damon grabbed her hips as she bounces on top of him, her hair covered her face like clouds covering the shiny moon.

For a while, both of them were soaring in heaven as they find their pleasure within each other bodies.

Soon she can feel similar coil unfurling inside her as she rocked harder than ever. "Fuck! You are so hot!" He groaned and for once she felt truly powerful and beautiful.

Damon watched with awe as this beautiful creature finally found the courage to revel in pleasure. She then squeezes her inner muscle making him scream her name as they both climaxed within each other.

She felt herself collapse but somehow strong arms embrace her and prepped her face with kisses and she was so sated to question this affectionate gesture.

For a while they stayed in each other arms but then he gently lifts her off him as he said. "I'm going to wash up." He then kissed her and then head towards the washroom.

Elena who was still smiling (like a silly girl who just had the best sex of her life) decide to dress up and call her friend so she can thank her when suddenly she hears her room bell rang.

"Who is there?" She asks feeling confused because she didn't call for room service.

"Elena! You there? Open up please!"

Realizing it was Rebekah she quickly wore a white hotel robe before heading to open her door.

There she saw a pissed off Rebekah glaring at some guy who was dressed in black.

"Bex? What are you doing here? I thought I was forbidden to call you until the next morning."

She looked extremely guilty as she punches the standing beside her. "This is all your fault!" She scolds him before turning to face her. "Elena I'm so sorry!"

"For what? In fact, you should be happy because not only your plan work but it also gave me the best night of my life."

"What are you talking about?"

But just then bathroom door open as Damon strolled out with only a white towel wrapped around him.

Damon was hoping to have round two with his gorgeous girl before treating her with dinner but those plans go in the drain when he saw a blonde woman and man staring at him with wide eyes while Elena beam at them.

"Oh! there you are. Rebekah, can you please tip Mr Salvatore extra? Because he really did a great job."

"Excuse me?" Damon asks taken aback by her words.

Meanwhile, Rebekah was staring at them with horrified eyes as her clueless friend continue. "Don't be shy Damon. You make one happy satisfied customer today and My friend will make sure to give you more money than your price."

Damon felt his mouth hung open and apparently the blonde girl understand something out of this nonsense because she finally intervenes. "Elena. Umm, don't start to freak out but this is not the guy I hire for you."

Elena who was still smiling start laughing at her friend's joke. "Ya right! You told me that your male escort will be dressed in black and approach me with a red rose, and even though he was late Damon finally showed up."

While Rebekah was still shaking her head, Damon finally got up with what really happened.

He felt his heartbreak more for this girl who thought her only way to get pleasure is to pay for it.

"Elena! Listen to me, please. I hire this guy. This idiot Tyler who got himself stuck in traffic and get late for two hours!"

They watched as her gaze jumps from all three of them before landing it on Damon in confusion. "But you said you haven't done this thing in four years?"

"I meant dating. Its been four years since my wife passed away and tonight you were the first girl I approach since her." He finally explains himself and now he wondered if he did clear things earlier then they would not be standing in this mess.

"You choose to approach me? Why?" She asks while stepping closer to him.

"Because my heart guides me to you." He admitted and then she turned away as she walked towards her friend.

Damon felt sad as he was sure she will leave him but then she hugged her friend. "Thanks, Bex, this stupid idea finally gave me my courage.

Rebekah smile and hugged her back. "Welcome to reality Gilbert."

With that, she waves at them and grabs Tyler's arm. "You come with me so I can get benefit out of my money."

Elena laughed while closing the door behind her.

Turning around she walked towards Damon and stopped a few steps away from him. "So you are not a male escort?"

She watched his eyes widened in shock as he shakes his head. "I am in the construction business, you can check me out.." But his rest of words cut off as she happily jumps into his arms and kisses him passionately.

After a few minutes, she gave him a happy sigh as she said. "I'm so glad you are not escort although you can have a bright future in that career."

They both laughed and then she squeals as they dropped on top of the bed.

He kissed her soundlessly before pulling away. "I can consider it if you will be my only client."

"Deal." She then gave him a playful command. "Now get on with it because you have to make up for a decade worth of sex."

With one flick both her robe and Damon's towel was on the floor as he promised. "Oh baby, I will spend my entire life making up to you."

And so he did not just for one night on Valentine 's Day but he loves and cherished her for rest of their days and nights.

**Notes for the Chapter:**

> Author's Notes.
> 
> Here you go, I hope you like this fluffy but from my heart two-shot. Please send me your reviews and motivate me to write more and more.

**Author's Note:**

> Author's Notes.
> 
> Here you go, the first chapter of this two-shot. The second half of this story will be updated within the day so send me as many reviews to motivate me to write more and fast.


End file.
